Catalysts for oxidative coupling of phenols

Abstract

Self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous cobalt-containing catalyst.

What is claimed is: 
     
       1. A process for preparing by an oxidation coupling reaction a carbon-carbon coupled or carbon-oxygen coupled condensation product of a substituted phenol of the formula ##STR2## wherein each R is hydrogen, halogen or R 1 , and each R 1  is a substituent having up to 10 carbons selected from the group consisting of hydrocarbon, halohydrocarbon and hydrocarbonoxy comprising contacting the substituted phenol with an oxygen-containing gas under oxidative coupling conditions in the presence of a heterogeneous catalyst comprising cobalt present in an oxidation state suitable for forming oxidatively coupled reaction products. 
     
     
       2. A process according to claim 1 wherein the substituted phenol is a 2,6-dialkyl phenol. 
     
     
       3. A process according to claim 1 wherein the catalyst comprises an oxide of cobalt. 
     
     
       4. A process according to claim 1 wherein the catalyst additionally comprises an oxide of copper. 
     
     
       5. A process according to claim 3 wherein the catalyst is supported by an inert supportive means. 
     
     
       6. A process according to claim 5 wherein the inert supportive means is alumina, carbon, silica, diatomaceous earth or clay. 
     
     
       7. A process according to claim 3 wherein the catalyst consists essentially of a mixture of the oxides of cobalt and copper. 
     
     
       8. A process according to claim 1 or 7 wherein an inert liquid reaction medium is also present. 
     
     
       9. A process according to claim 8 wherein the inert liquid reaction medium is a polar compound. 
     
     
       10. A process according to claim 9 wherein the inert liquid reaction medium is methanol. 
     
     
       11. A process according to claim 1 which is conducted at a temperature from about 30° C. to about 200° C. and at an elevated pressure of up to about 500 psig. 
     
     
       12. A process according to claim 2 wherein the substituted phenol is 2,6-ditertiary butyl phenol and the condensation product is 3,3', 5,5'-tetratertiarybutyl diphenoquinone. 
     
     
       13. The process according to claim 12 wherein the 3,3', 5,5'-tetratertiarybutyl diphenoquinone is thereafter reduced. 
     
     
       14. The process according to claim 13 wherein the reduction is accomplished by contacting the 3,3', 5,5'-tetratertiarybutyl diphenoquinone with hydrogen-containing gas in the presence of a heterogeneous hydrogenation catalyst at a temperature from about 25° C. to about 150° C. and pressures from about atmospheric to about 100 psig.